Every Celebrity Romance You Don’t Remember, But Now Will Never Forget Again

Every Celebrity Romance You Don’t Remember, But Now Will Never Forget Again

If we’ve heard it once, we’ve heard it a hundred times in every celebrity interview, A-listers like to date each other because they say it makes it easier if their partner understands the demands of their job. We get it. But just because they were dating within “the biz” doesn’t guarantee that their love was built to last. They may have dated long ago, and a few couples might have even forgotten they were ever in a romance, but we just can’t. We think about that time Cher dated a certain action star at least once a week, and now you will too.

1. Jessica Biel & Chris Evans

We have no idea how these two first met, but since it was sometime in 2001, we’re going to imagine it was backstage at TRL. Chris Evans was just at the start of his Hollywood career, while Jessica Biel was post-Seventh Heaven when these two started showing up side-by-side at VH1 music video awards and movie premiere red carpets.

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Chris and Jessica went on to date for five more years, telling different interviewers that they regularly discussed the possibility of marriage. In that time they starred in two films together, Cellular and then London – a film about the dissolution of a couple. Woefully, life imitated art when these two split up soon after.

2. Alanis Morissette & Ryan Reynolds

Canadian national treasures Alanis Morissette and Ryan Reynolds first met in 2002 at Drew Barrymore’s birthday party, and for a time it seemed like destiny. After dating for two years the couple became engaged in 2004, but a walk down the aisle wasn’t in the cards.

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The two split up sometime later, an event which served as the primary source of inspiration for Morissette’s seminal breakup album “Flavors of Entanglement.” All in all, the dissolution of this couple led to two happy marriages (Reynolds to Blake Lively and Morissette to Mario Treadway) and one amazing album, so we’d call that breakup a success — isn’t it ironic?

3. Natalie Portman & Moby

Have you ever heard the one about Natalie Portman and Moby? Actually, this isn’t the setup to a joke, although these two did surprise everyone when word got out that they were an item back in 2001. Their fledgling relationship didn’t last all that long, and perhaps Padme Amidala is to blame.

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Portman’s role as Luke Skywalker’s mother Padme Amidala only a few years prior meant that their relationship received considerable scrutiny from Star Wars superfans. Moby would later admit of their romance, “…it’s made me a target of a lot of nerd wrath.” Seems these two were just a spark, not written in the stars.

4. Bradley Cooper & Renee Zellweger

Meeting as so many Hollywood couples do — on set, Bradley Cooper and Renee Zellweger began dating after starring in the 2006 thriller Case 39. The film’s release was delayed until 2010, but by the time the stars were making promotional appearances, they had reportedly been living together for a year.

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All along, the notoriously private pair never acknowledged anything in the press, despite many snaps of vacations together, date nights, and meeting the family. Bradley’s increasingly hectic work schedule as he made the move from supporting actor to leading man was cited as the main crux of their uncoupling by March 2011.

5. Ashton Kutcher & January Jones

Before he was one half of the real life That 70s Show couple of our dreams (Jackie and Kelso forever), Ashton Kutcher was an Abercrombie & Fitch model from Iowa, with hopes for Hollywood. Similarly, January Jones moved from South Dakota to Los Angeles to pursue her acting career, while making ends meet as an Abercrombie & Fitch model.

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They were a modeling match, and proceeded to make for a photogenic pair from 1998 until 2001. Despite some rumors surrounding Ashton’s attitude toward January’s acting aspirations, Jones has long since cleared the air and explained she’s super happy for her amicable ex.

6. Madonna & Dennis Rodman

What did NBA basketball star of the Spurs, Dennis Rodman have in common with the Princess of Pop, Madonna? To be honest, we’re not entirely sure, but love knows no bounds, opposites attract, and all those other adages applied during the two month period Madonna and Dennis Rodman dated back in 1994.

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It may have only been for an all-too-brief bit of time, but thank goodness for the photographers who captured the pair’s public outings, and moreover, their outfits. Rodman and Madonna had a penchant for amazing, over-the-top getups we’ll just never get over, even after they got over their short-lived romance.

7. Tom Cruise & Cher

You would think that this couple would be easy to remember, just forever stamped at the forefront of our collective conscience – but somehow the May-December romance of Cher and Tom Cruise is too often forgotten. So how on earth did these two find each other in this mixed up world? A wedding.

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And it wasn’t any old wedding, Tom Cruise and Cher first met at Madonna’s 1985 wedding to Sean Penn. While there was a bit of a spark then, it wasn’t until they were both invited to the White House to discuss dyslexia (something they have in common) that a romance blossomed. Cher still smiles wistfully whenever she reminisces on their relationship, as do we.

8. Justin Timberlake & Jenna Dewan

When Justin Timberlake and Britney Spears’ relationship went south, thereby crushing every pop-loving teen’s dreams (goodbye matching denim outfits, we’ll always miss you), we wondered, if those two couldn’t make it work could anyone? Well, little lovelorn Justin did find romance again, with his then-backup dancer Jenna Dewan.

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Although they’d both ultimately go on to marry other A-listers — Timberlake and Jessica Biel have been married since 2012, Dewan and Channing Tatum were married from 2009-2018 — Jenna and Justin were together for a time. As two extremely talented dancers, our only wish is for a video of the one-time couples’ sweet moves on stage, at least for posterity’s sake.

9. Cameron Diaz & Jared Leto

If Cameron Diaz’s current marriage to rocker Benji Madden may seem surprising to some, the Hollywood darling already had experience dating musicians. Golden haired golden couple of the late 90s and early aughts Cameron Diaz and Jared Leto were a match made in matching haircut heaven.

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The 30 Seconds To Mars frontman Jared Leto calls Cameron one of his first serious girlfriends. The couple began dating in 1999, and were widely reported to have gotten engaged sometime during their four year romance. Although they’d ultimately part ways, we still recommend looking back on photos of the photogenic couple for some sweet 90s style inspiration.

10. Julia Roberts & Liam Neeson

We don’t blame you for having forgotten this couple, or for having no idea that they’d ever even dated. Meeting on the set of dramedy film Satisfaction in 1988, a fresh to Hollywood Julia Roberts fell for costar Liam Neeson almost immediately.

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With a sixteen year age difference between them, Neeson was in his mid-30s and far more familiar with the business than a 19-year old Roberts. Already a successful actor, Neeson surely impressed the impressionable Roberts and the two reportedly moved in together within weeks of meeting. More than an infatuation, the couple lasted two years before amicably absolving their coupledom.

11. Kate Hudson & Alex Rodriguez

Kate Hudson and Alex Rodriguez were rumored to have met at the grand re-opening of the Fontainebleau Miami Beach Hotel in 2008, while Rodriguez was newly romancing none other than Madonna (remember them?!). A few months later, A-Rod and Madonna were no more, but Hudson was seen popping up at the athlete’s baseball games (Let’s go Yankees!).

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Although neither party confirmed the pairing in the press, a memorable stadium kiss seemed to say it all. However, Hudson’s interest in America’s favorite pastime passed pretty quickly when the couple parted ways after a few months. Presently, Hudson has a brand new baby girl, and A-Rod’s found the perfect partner in JLo.

12. Nicole Kidman & Lenny Kravitz

Before Nicole Kidman starred alongside Zoe Kravitz on Big Little Lies, she was was starring in a real-life love story with Zoe’s father, famed rocker Lenny Kravitz. Kidman and Kravitz first started quietly dating in 2002, quickly moving in together. The twosome split in 2003, but a few years later Kidman confessed that at the time, they were secretly engaged.

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Since then Kravitz and Kidman have both said that they weren’t really ready for a walk down the aisle, but are happy to have been reunited through Big Little Lies. From fiancé and pseudo-stepmom to co-star, Kidman and Kravitz are keeping it all in the family.

13. Michael Keaton & Courteney Cox

We’re not sure how this relationship could have ever been forgotten when Courteney Cox herself once said about her one-time beau Michael Keaton “It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met.”

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Keaton and Cox were no passing fling. Getting together in 1989, the super private pair were together as Keaton took on the caped crusader in Tim Burton’s Batman movies, and for the start of Cox’s career on Friends. After six years and two iconic roles, the two went their separate ways, but now that you know, you’ll never forget that Monica once dated Batman.

14. Drew Barrymore & David Arquette

If you don’t remember this pairing you’re not alone, Drew Barrymore can hardly recall dating David Arquette too — they were both teens at the time! There was obviously no animosity after they split, especially since the two went on to star as siblings in 1999’s Never Been Kissed.

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Arquette described their dating life at such a young age, saying “We used to run around and just be silly.” In honor of the 20th anniversary of Never Been Kissed, Barrymore and Arquette have both been throwing it back to their time on set, where it sounds like similar silliness ensued. We love exes who still get along.

15. Sandra Bullock & Ryan Gosling

She’s America’s Sweetheart, and after appearing in The Notebook, he’ll forever be our dream boyfriend, with those credentials a romance between Sandra Bullock and Ryan Gosling makes so much sense. Meeting on the set of the thriller Murder By Numbers in 2002, Sandra was sixteen years Gosling’s senior.

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Age is only a number after all, and even though these two couldn’t make it work long-term, they worked quite a few red carpets together, from the stateside premiere of the film on which fate brought them together, all the way to the Cannes Film Festival. After the better part of two years, Bullock and Gosling said farewell, but we’ll always remember them fondly.

16. Pink & Joey Fatone

Pink and Joey Fatone dated and our pop loving selves didn’t know about it, how can that be? Probably because it was just one date, but it was all so sweet and sentimental, we’ll build up an entire romance out of it in our minds.

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It started when a young Pink was on tour with boyband of the decade (this isn’t the time for a Backstreet Boys vs. N*SYNC debate) and Joey Fatone formed a schoolboy style crush. After asking her father for permission to take her on a date, the pop music pair went to Friendly’s for an ice cream. It might not have been much, but what it was couldn’t be cuter.

17. Matt Damon & Winona Ryder

Everyone remembers when Winona Ryder and Johnny Depp were the It Couple of Tinseltown, but what about her romance with a fresh-faced Matt Damon? Introduced by Gwyneth Paltrow who was dating Ben Affleck at the time (never forget) we love the idea of the four of them going out on double dates.

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Damon and Ryder were together from 1997 to 2000, before deciding to downgrade their relationship status to just friends (coincidentally, Ben and Gwyn’s relationship lasted just as long). Years after their drama-free romantic dissolution, Ryder would describe Damon as the nicest guy and explained that the two are still “on good terms.” Aren’t they sweet.

18. Sheryl Crow & Owen Wilson

All she wanted to do was have some fun, and we’re hoping Sheryl Crow’s relationship with Owen Wilson was just that (most of the time). So, as is often the case in Hollywood, these two met on the set of the 1999 film The Minus Man and flew headfirst into a relationship.

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Though neither talked about their coupling much to the press, they made some high profile red carpet appearances together before calling time on their romance in 2001. Crow wrote the bittersweet ballad “Safe and Sound” after their split, and dedicated it to Wilson. Breakups can be sad, but Sheryl sings it best, “There’s beauty in release.”

19. Fiona Apple & David Blaine

No sleight of hand or complex illusions at play, this pair was the real deal. While it’s unclear as to when exactly Fiona Apple and David Blaine started dating, by 1997 the songstress was singing Blaine’s praises to SPiN magazine, saying they were similar sorts of people – seems like an ideal start to a romantic partnership.

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We’re not sure what lead these two to split either, or when, but our super skilled cyber sleuthing has revealed sweet snaps of them together up through 1999. Whatever spell the twosome were under it seems to have worn off by or before 2000, but for the time Apple and Blaine were together, it was all magic.

20. Brooke Shields & Nicolas Cage

Not much is known about the approximately year long relationship between Brooke Shields and Nicolas Cage, but as one of the top models of the 80s, Shields caught Cage at just the right time. Fresh off his first few major film roles as leading man, the newly dating duo made their red carpet debut at the premiere of Moonstruck in 1987.

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Nicolas Cage was still quite young at the time, but we’d like to imagine he picked up a thing or two from his character in Moonstruck and used it to charm a similarly young Brooke Shields. Surely Cher passed on some wisdom on-set to her co-star Cage, right?

21. Kid Rock & Pamela Anderson

On-and-off between 2001-03, Pamela Anderson and Kid Rock kept coming back together like moths to a flame, before seemingly call it off for good. But! By July 2006 the twosome surprised us all when they were not only back together, but married in a sudden ceremony on a yacht in St. Tropez.

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For their summer nuptials the groom wore a white t-shirt and baseball cap, while the bride wore a white bikini. Alas, these two came apart as quickly as they came together, splitting up in earnest in November of that year. In the wise words of Lao Tzu, “The flame that burns twice as bright burns half as long.”

22. Joaquin Phoenix & Liv Tyler

It’s hard to forget your first love, and doubly hard when your first love is a major Hollywood heavyweight. Luckily for Liv Tyler and Joaquin Phoenix, they still like each other a whole lot, and have each taken their turn offering up praise for their former partner.

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Meeting sometime in 1995, Tyler was only 18 and Joaquin was 21 when they embarked on a romance. The couple would be together for three years, and even though their relationship didn’t last, their time together made an impression, as Tyler attests, “He was my first love…he’s a huge part of even my sense of humor.” As far as first loves go, they got it really right.

23. Paula Abdul & John Stamos

At first when you learn that Paula Abdul and John Stamos dated you are utterly stunned, “What? When!” But another minute to process this new information and suddenly, well, doesn’t their dating make so much sense? Two icons of the 80s and 90s were an item and it just feels right.

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It may not have been for very long, but Stamos accompanied Abdul to the Grammys in 1990, and thank goodness because no one but John Stamos could have held his own beside her gold dress. Since the two are still on good terms today, and Stamos is an accomplished drummer, might we suggest these two reunite in the studio?

24. Christina Applegate & Brad Pitt

Trying to come up with something a little different from the tried and true dinner or drinks for a first date? Ask Christina Applegate – the Married…With Children star famously brought up-and-coming actor Brad Pitt to the MTV Music Video Awards in 1989 as a first (and sadly last) date.

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Even as they struck some cute poses on the red carpet, their romance was destined to be short lived…really really short lived. Applegate apparently wasn’t all that taken with young Brad Pitt, and left their date halfway through. Awkward. Although Applegate and Pitt found love again, we wonder what might have been had they given it another go.

25. Angelina Jolie & Jonny Lee Miller

Long before our hearts were broken by the demise of Brangelina, and before the head-scratcher that was Angelina and Billy Bob Thornton, there was Angie and Jonny Lee Miller. The two met on the set of the 1995 film Hackers, and half a year after they’d called cut, the two were wed in a quiet civil ceremony.

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Our girl Angie wore rubber pants and a white t-shirt with “Jonny Lee Miller” written on the back in her own blood, but for a surprisingly sweet reason, “You can sacrifice a little to make it really special.” Although they separated in 1997, there’s no bad blood, and Angie and Jonny are still good friends.

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